[(1S,2S,3R,4R)-3-Hydr-oxy-4,7,7-tri-methyl-bicyclo-[2.2.1]heptan-2-yl]methyl[(E)-3-(trimethyl-silyl)prop-2-enyl]selen-onium bromide.

The title compound, a seleno-nium bromide, C(17)H(33)OSeSi(+)·Br(-), was obtained from the reaction of enanti-omerically pure 4,7,7-trimethyl-2-methyl-selanylbicyclo-[2.2.1]heptan-3-ol and (3-bromopropen-yl)trimethyl-silane in acetone. Due to the chiral bicyclic substituent, the crystal structure is not centrosymmetric and has no symmetry plane, with four chiral C atoms in the cation. The asymmetric unit contains one seleno-nium cation and one bromide anion. C-H⋯Br and O-H⋯Br hydrogen bonds link the ions, forming a one-dimensional R-helical chain-like supra-molecular structure.

Related literature

For related literature, see: Li et al. (2005 ▶); Goodridge et al. (1988 ▶); Reich et al. (1975 ▶); Ye et al. (2002 ▶).

Experimental

Crystal data

C17H33OSeSi+·Br−

M = 440.39

Monoclinic,

a = 7.555 (2) Å

b = 10.023 (2) Å

c = 14.423 (3) Å

β = 101.29 (3)°

V = 1071.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 3.67 mm−1

T = 291 (2) K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.35, T max = 0.41

4460 measured reflections

3374 independent reflections

1732 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.102

S = 1.07

3374 reflections

170 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.74 e Å−3

Absolute structure: Flack (1983 ▶), 1140 Friedel pairs

Flack parameter: 0.01 (2)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016863/im2070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016863/im2070Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H33OSeSi+·Br–	F000 = 452
Mr = 440.39	Dx = 1.366 Mg m−3
Monoclinic, P2(1)	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 895 reflections
a = 7.555 (2) Å	θ = 2.1–24.5º
b = 10.023 (2) Å	µ = 3.67 mm−1
c = 14.423 (3) Å	T = 291 (2) K
β = 101.29 (3)º	Bloc, colourless
V = 1071.0 (4) Å3	0.30 × 0.26 × 0.24 mm
Z = 2

Bruker SMART Apex CCD diffractometer	3374 independent reflections
Radiation source: sealed tube	1732 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 291(2) K	θmax = 26.0º
phi and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.35, Tmax = 0.41	k = 0→12
4460 measured reflections	l = 0→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.64 e Å−3
3374 reflections	Δρmin = −0.74 e Å−3
170 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1140 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (2)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.32321 (7)	1.05851 (10)	0.09364 (5)	0.0584 (2)
C1	0.6248 (8)	0.4347 (6)	0.3285 (4)	0.0404 (14)
H1A	0.6335	0.3442	0.3079	0.061*
H1B	0.5363	0.4400	0.3679	0.061*
H1C	0.7399	0.4630	0.3637	0.061*
C2	0.7389 (6)	0.5504 (10)	0.2095 (4)	0.0425 (13)
H2A	0.8154	0.6083	0.2529	0.064*
H2B	0.7085	0.5928	0.1488	0.064*
H2C	0.8013	0.4683	0.2036	0.064*
C3	0.5706 (8)	0.5219 (6)	0.2454 (5)	0.0498 (18)
C4	0.4232 (11)	0.4559 (8)	0.1682 (5)	0.0445 (19)
H4	0.4615	0.3724	0.1428	0.053*
C5	0.3867 (6)	0.5695 (8)	0.0960 (4)	0.0361 (12)
H5	0.4822	0.5710	0.0588	0.043*
C6	0.3996 (9)	0.6917 (8)	0.1552 (5)	0.0398 (16)
H6	0.4963	0.7496	0.1422	0.048*
C7	0.4459 (9)	0.6398 (7)	0.2553 (4)	0.0473 (15)
C8	0.2804 (6)	0.5707 (9)	0.2761 (4)	0.0406 (14)
H8A	0.1744	0.6264	0.2578	0.049*
H8B	0.2955	0.5499	0.3428	0.049*
C9	0.2627 (8)	0.4411 (7)	0.2161 (5)	0.0460 (15)
H9A	0.2728	0.3619	0.2555	0.055*
H9B	0.1499	0.4384	0.1704	0.055*
C10	0.5215 (9)	0.7500 (7)	0.3273 (5)	0.047
H10A	0.6407	0.7741	0.3196	0.071*
H10B	0.5262	0.7175	0.3903	0.071*
H10C	0.4444	0.8269	0.3166	0.071*
C11	0.2014 (9)	0.3828 (7)	−0.0510 (5)	0.043
H11A	0.3020	0.3955	−0.0816	0.064*
H11B	0.0971	0.3576	−0.0970	0.064*
H11C	0.2294	0.3137	−0.0043	0.064*
C12	0.2030 (8)	0.6908 (7)	−0.0809 (4)	0.0415 (15)
H12A	0.1683	0.7780	−0.0614	0.050*
H12B	0.3310	0.6926	−0.0820	0.050*
C13	0.0925 (8)	0.6561 (7)	−0.1810 (4)	0.0430 (15)
H13	−0.0322	0.6663	−0.1918	0.052*
C14	0.1643 (8)	0.6141 (6)	−0.2502 (4)	0.0385 (13)
H14	0.2893	0.6068	−0.2395	0.046*
C15	−0.0572 (9)	0.3993 (7)	−0.3683 (5)	0.047
H15A	−0.1696	0.4027	−0.3468	0.071*
H15B	0.0262	0.3436	−0.3267	0.071*
H15C	−0.0771	0.3631	−0.4311	0.071*
C16	−0.1393 (8)	0.6949 (7)	−0.4057 (5)	0.041
H16A	−0.2022	0.6764	−0.4689	0.061*
H16B	−0.0837	0.7813	−0.4039	0.061*
H16C	−0.2231	0.6937	−0.3636	0.061*
C17	0.1943 (7)	0.5796 (7)	−0.4543 (4)	0.049
H17A	0.2631	0.4987	−0.4522	0.073*
H17B	0.2746	0.6536	−0.4372	0.073*
H17C	0.1259	0.5926	−0.5171	0.073*
O1	0.2297 (6)	0.7626 (5)	0.1376 (3)	0.0473 (11)
H1D	0.248 (10)	0.845 (8)	0.125 (5)	0.057*
Se1	0.15165 (6)	0.54982 (7)	0.01059 (4)	0.04094 (15)
Si1	0.03564 (18)	0.5673 (2)	−0.36882 (11)	0.0395 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.0503 (3)	0.0494 (4)	0.0775 (5)	−0.0034 (4)	0.0172 (3)	−0.0074 (5)
C1	0.043 (3)	0.043 (4)	0.040 (3)	0.000 (3)	0.020 (3)	0.000 (3)
C2	0.031 (2)	0.049 (3)	0.043 (3)	−0.012 (4)	−0.0060 (19)	−0.021 (5)
C3	0.038 (3)	0.046 (4)	0.053 (4)	−0.019 (3)	−0.020 (3)	0.003 (3)
C4	0.059 (4)	0.038 (4)	0.034 (4)	−0.005 (3)	0.004 (3)	0.008 (3)
C5	0.035 (2)	0.037 (3)	0.035 (3)	0.019 (3)	0.0062 (18)	0.005 (3)
C6	0.034 (3)	0.048 (4)	0.040 (4)	−0.005 (3)	0.013 (3)	0.003 (3)
C7	0.052 (3)	0.047 (3)	0.037 (4)	0.001 (3)	−0.003 (3)	0.006 (3)
C8	0.042 (2)	0.049 (4)	0.035 (3)	0.016 (3)	0.017 (2)	−0.009 (3)
C9	0.034 (3)	0.046 (4)	0.055 (4)	−0.004 (3)	0.004 (3)	0.005 (3)
C10	0.049	0.049	0.049	0.000	0.021	0.000
C11	0.044	0.044	0.044	0.000	0.018	0.000
C12	0.039 (3)	0.051 (4)	0.036 (3)	0.020 (3)	0.012 (3)	0.009 (3)
C13	0.045 (3)	0.048 (4)	0.033 (3)	0.005 (3)	0.002 (3)	0.014 (3)
C14	0.044 (3)	0.044 (3)	0.029 (3)	−0.004 (2)	0.012 (2)	−0.002 (3)
C15	0.049	0.049	0.049	0.000	0.021	0.000
C16	0.043	0.043	0.043	0.000	0.020	0.000
C17	0.050	0.050	0.050	0.000	0.020	0.000
O1	0.046 (2)	0.049 (3)	0.038 (2)	−0.010 (2)	−0.0126 (19)	0.003 (2)
Se1	0.0358 (2)	0.0516 (3)	0.0339 (3)	0.0028 (4)	0.00292 (19)	0.0086 (4)
Si1	0.0420 (7)	0.0402 (9)	0.0380 (8)	0.0077 (9)	0.0119 (6)	−0.0030 (10)

Br1—O1	3.143 (5)	C10—H10B	0.9600
C1—C3	1.475 (9)	C10—H10C	0.9600
C1—H1A	0.9600	C11—Se1	1.965 (7)
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C2—C3	1.492 (8)	C11—H11C	0.9600
C2—H2A	0.9600	C12—C13	1.560 (9)
C2—H2B	0.9600	C12—Se1	2.022 (6)
C2—H2C	0.9600	C12—H12A	0.9700
C3—C7	1.535 (9)	C12—H12B	0.9700
C3—C4	1.559 (9)	C13—C14	1.295 (8)
C4—C9	1.515 (10)	C13—H13	0.9300
C4—C5	1.531 (10)	C14—Si1	1.855 (6)
C4—H4	0.9800	C14—H14	0.9300
C5—C6	1.484 (10)	C15—Si1	1.825 (7)
C5—Se1	1.963 (5)	C15—H15A	0.9600
C5—H5	0.9800	C15—H15B	0.9600
C6—O1	1.446 (8)	C15—H15C	0.9600
C6—C7	1.510 (9)	C16—Si1	1.842 (7)
C6—H6	0.9800	C16—H16A	0.9600
C7—C8	1.510 (9)	C16—H16B	0.9600
C7—C10	1.546 (9)	C16—H16C	0.9600
C8—C9	1.552 (10)	C17—Si1	1.884 (5)
C8—H8A	0.9700	C17—H17A	0.9600
C8—H8B	0.9700	C17—H17B	0.9600
C9—H9A	0.9700	C17—H17C	0.9600
C9—H9B	0.9700	O1—H1D	0.87 (8)
C10—H10A	0.9600
C3—C1—H1A	109.5	C7—C10—H10A	109.5
C3—C1—H1B	109.5	C7—C10—H10B	109.5
H1A—C1—H1B	109.5	H10A—C10—H10B	109.5
C3—C1—H1C	109.5	C7—C10—H10C	109.5
H1A—C1—H1C	109.5	H10A—C10—H10C	109.5
H1B—C1—H1C	109.5	H10B—C10—H10C	109.5
C3—C2—H2A	109.5	Se1—C11—H11A	109.5
C3—C2—H2B	109.5	Se1—C11—H11B	109.5
H2A—C2—H2B	109.5	H11A—C11—H11B	109.5
C3—C2—H2C	109.5	Se1—C11—H11C	109.5
H2A—C2—H2C	109.5	H11A—C11—H11C	109.5
H2B—C2—H2C	109.5	H11B—C11—H11C	109.5
C1—C3—C2	106.0 (5)	C13—C12—Se1	108.2 (4)
C1—C3—C7	117.3 (6)	C13—C12—H12A	110.1
C2—C3—C7	117.8 (6)	Se1—C12—H12A	110.1
C1—C3—C4	112.0 (5)	C13—C12—H12B	110.1
C2—C3—C4	111.8 (6)	Se1—C12—H12B	110.1
C7—C3—C4	91.6 (5)	H12A—C12—H12B	108.4
C9—C4—C5	109.2 (6)	C14—C13—C12	123.8 (5)
C9—C4—C3	103.9 (6)	C14—C13—H13	118.1
C5—C4—C3	100.3 (5)	C12—C13—H13	118.1
C9—C4—H4	114.0	C13—C14—Si1	124.7 (5)
C5—C4—H4	114.0	C13—C14—H14	117.6
C3—C4—H4	114.0	Si1—C14—H14	117.6
C6—C5—C4	103.8 (5)	Si1—C15—H15A	109.5
C6—C5—Se1	113.2 (4)	Si1—C15—H15B	109.5
C4—C5—Se1	111.9 (5)	H15A—C15—H15B	109.5
C6—C5—H5	109.3	Si1—C15—H15C	109.5
C4—C5—H5	109.3	H15A—C15—H15C	109.5
Se1—C5—H5	109.3	H15B—C15—H15C	109.5
O1—C6—C5	110.4 (5)	Si1—C16—H16A	109.5
O1—C6—C7	111.6 (5)	Si1—C16—H16B	109.5
C5—C6—C7	104.1 (6)	H16A—C16—H16B	109.5
O1—C6—H6	110.2	Si1—C16—H16C	109.5
C5—C6—H6	110.2	H16A—C16—H16C	109.5
C7—C6—H6	110.2	H16B—C16—H16C	109.5
C6—C7—C8	107.5 (5)	Si1—C17—H17A	109.5
C6—C7—C3	102.0 (5)	Si1—C17—H17B	109.5
C8—C7—C3	102.2 (5)	H17A—C17—H17B	109.5
C6—C7—C10	112.5 (6)	Si1—C17—H17C	109.5
C8—C7—C10	114.0 (6)	H17A—C17—H17C	109.5
C3—C7—C10	117.4 (5)	H17B—C17—H17C	109.5
C7—C8—C9	105.0 (5)	C6—O1—Br1	105.8 (4)
C7—C8—H8A	110.8	C6—O1—H1D	109 (5)
C9—C8—H8A	110.8	C5—Se1—C11	98.0 (3)
C7—C8—H8B	110.8	C5—Se1—C12	94.2 (3)
C9—C8—H8B	110.8	C11—Se1—C12	102.9 (3)
H8A—C8—H8B	108.8	C15—Si1—C16	112.8 (3)
C4—C9—C8	100.5 (5)	C15—Si1—C14	111.2 (3)
C4—C9—H9A	111.7	C16—Si1—C14	107.9 (3)
C8—C9—H9A	111.7	C15—Si1—C17	110.9 (3)
C4—C9—H9B	111.7	C16—Si1—C17	106.1 (3)
C8—C9—H9B	111.7	C14—Si1—C17	107.6 (3)
H9A—C9—H9B	109.4

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Br1	0.87 (8)	2.28 (8)	3.143 (5)	175 (7)
C5—H5···Br1i	0.98	2.88	3.827 (5)	164
C11—H11C···Br1ii	0.96	2.94	3.874 (7)	165
C12—H12B···Br1i	0.97	2.97	3.855 (5)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯Br1	0.87 (8)	2.28 (8)	3.143 (5)	175 (7)
C5—H5⋯Br1i	0.98	2.88	3.827 (5)	164
C11—H11C⋯Br1ii	0.96	2.94	3.874 (7)	165
C12—H12B⋯Br1i	0.97	2.97	3.855 (5)	152

Symmetry codes: (i) ; (ii) .